Deck 9: Alcohols, Ethers, and Related Compounds

Question 1

Which of the following compounds has the highest boiling point?

A)I
B)II
C)III
D)IV

Answer 1

II

Question 2

What is the IUPAC of the following compound?

A)5-Hydroxy-3-methyl-1-pentene
B)3-Methyl-5-penten-1-ol
C)3-Methyl-1-penten-5-ol
D)3-Methyl-4-penten-1-ol

Answer 2

3-Methyl-4-penten-1-ol

Question 3

What is the IUPAC of the following compound?

A)3,3,6-Trimethylcyclohexanol
B)2,5,5-Trimethylcyclohexanol
C)1,4,4-Trimethyl-2-cyclohexanol
D)1,1,4-Trimethyl-2-cyclohexanol

Answer 3

2,5,5-Trimethylcyclohexanol

Question 4

What is the IUPAC of the following compound?

A)1,2-Epoxy-2-methylcyclopentane
B)1,2-Epoxy-1-methylcyclopentane
C)1,2-Epoxy-1-methylpentane
D)1,2-Epoxy-2-methylpentane

Question 5

Which of the following compounds are epoxides?

A)Only I and III
B)Only III and IV
C)Only I, III, and IV
D)I, II, III, and IV

Question 6

Rank the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

A)III < II < I < IV
B)II < III < I < IV
C)IV < I < II < III
D)I < II < III < IV

Question 7

Which of the following explains why epoxides are much more reactive than ethers?

A)The C-O-C bond angle of an epoxide is 109°, making epoxides to have angle strain.
B)The oxygen atom of an epoxide is sp² hybridized.
C)The C-O-C bond angle of an epoxide is 120°, making epoxides to have angle strain.
D)The C-O-C bond angle of an epoxide is 60°, making epoxides to have angle strain.

Question 8

What is the IUPAC of the following compound?

A)Ethoxyoctane
B)5-Ethoxyoctane
C)4-Ethoxyoctane
D)Ethyl octyl ether

Question 9

What is the IUPAC of the following compound?

A)1,1-Dimethyloxirane
B)2-Methylpropylane
C)2-Methylpropylene oxide
D)2,2-Dimethyloxirane

Question 10

What is the common name of the following compound?

A)Methyl vinyl ether
B)Allyl methyl ether
C)Propenyl methyl ether
D)Methylene propylene ether

Question 11

What is the common name of the following compound?

A)Methyl sec-butyl ether
B)Isobutyl methyl ether
C)sec-Butyl methyl ether
D)Butyl methyl ether

Question 12

What is the IUPAC of the following compound?

A)(S)-2,2-Dimethyl-3-pentanol
B)(R)-2,2-Dimethyl-3-pentanol
C)(R)-4,4-Dimethyl-3-pentanol
D)(S)-1-tert-Butyl-1-propanol

Question 13

What is the common name of the following compound?

A)Isobutyl isopropyl ether
B)Diisobutyl ether
C)Di-sec-butyl ether
D)Diisopropyl ether

Question 14

Which of the following compounds is (are) symmetrical ethers?

A)Only I
B)Only IV
C)Only III and IV
D)Only I, III, and IV

Question 15

Which of the following compounds is (are) secondary alcohols?

A)Only I
B)Only II
C)Only II and III
D)Only III and IV

Question 16

Which of the following compounds has the highest boiling point?

A)I
B)II
C)III
D)IV

Question 17

What is the IUPAC of the following compound?
(CH₃CH₂)₃COH

A)2-Ethyl-2-pentanol
B)2-Ethyl-3-pentanol
C)3-Ethyl-3-pentanol
D)2,2-Diethyl-1-butanol

Question 18

Which of the following compounds is (are) primary alcohols?

A)Only I
B)Only II
C)Only I and II
D)Only II and III

Question 19

What is the IUPAC of the following compound?

A)1,2-Epoxy-4-methylcyclohexane
B)3,4-Epoxy-1-methylcyclohexane
C)1,2-Epoxy-3-methylcyclohexane
D)1,2-Epoxy-5-methylcyclohexane

Question 20

Which of the following compounds are ethers?

A)Only I and II
B)Only III and IV
C)Only I, II, and III
D)I, II, III, and IV

Question 21

What is the major organic product obtained from the following sequence of reactions?

A)(R)-2-Methylpentanenitrile
B)(S)-2-Methylpentanenitrile
C)(±)-2-Methylpentanenitrile
D)trans-2-Butene

Question 22

What is the major organic product(s) obtained in the following reaction?

A)I
B)II
C)III
D)I and II

Question 23

What is the product of the following reaction?

A)I
B)II
C)III
D)IV

Question 24

Determine the product(s) of the following reaction.

A)Only I
B)Only II
C)Only III
D)Only II and III

Question 25

What is the major organic product obtained from the following reaction?

A)(±)-2-Chlorobutane
B)(R)-2-Chlorobutane
C)(S)-2-Chlorobutane
D)trans-2-Butene

Question 26

What are the major products obtained upon treatment of ethyl methyl ether with excess HBr?

A)Bromomethane and ethanol
B)Bromoethane and methanol
C)Bromoethane and bromomethane
D)Ethanol and methanol

Question 27

Determine the product(s) of the following reaction.

A)Only I
B)Only II
C)Only III
D)Only I and II

Question 28

Which of the following statements about carbocation rearrangement is not true?

A)A less stable carbocation can rearrange to a more stable carbocation by shift of a hydrogen atom.
B)A less stable carbocation can rearrange to a more stable carbocation by shift of an alkyl group.
C)1,2-Shifts convert a less stable carbocation to a more stable carbocation.
D)The migrating group in a 1,2-shift moves with one bonding electron.

Question 29

What is the major organic product obtained from the following sequence of reactions?

A)2-Methyl-1-butene
B)3-Methyl-3-butene
C)1-Chloro-2-methylbutane
D)1-Bromo-2-methylbutane

Question 30

Rank the alcohols in order of increasing reactivity when dehydrated with H₂SO₄, putting the least reactive first.

A)I < III < II
B)I < II < III
C)II < III < I
D)III < II < I

Question 31

Which of the following alcohols reacts the fastest with HCl to give the corresponding alkyl halide?

A)I
B)II
C)III
D)IV

Question 32

What is the best choice of reagent to accomplish the following transformation?

A)TsCl, pyridine
B)POCl₃, pyridine
C)HCl, ZnCl₂
D)NaOH

Question 33

What are the major products obtained upon treatment of tert-butyl methyl ether with excess HI?

A)tert-Butyl alcohol and iodomethane
B)tert-Butyl iodide and iodomethane
C)tert-Butyl alcohol and methanol
D)tert-Butyl iodide and methanol

Question 34

What is the best choice of reagent to accomplish the following transformation?

A)HCl
B)SOCl₂, pyridine
C)Cl₂
D)H₃O⁺, H₂O

Question 35

Which of the following would be a reasonable synthesis of 1-butanol?

A)I
B)II
C)III
D)IV

Question 36

Which of the following statements about a crown ether-cation complex is not true?

A)It is a host-guest complex.
B)The crown ether is the guest and the cation is the host.
C)The crown ether is the host and the cation is the guest.
D)The host-guest complex is soluble in nonpolar solvents.

Question 37

What is the major organic product obtained from the following reaction?

A)I
B)II
C)III
D)IV

Question 38

What is the best choice of reagent to accomplish the following transformation?

A)HCl
B)H₂SO₄
C)NaOH
D)TsCl, pyridine

Question 39

Which of the following would be a reasonable synthesis of 2-butanol?

A)I
B)II
C)III
D)IV

Question 40

What is the major organic product obtained from the following sequence of reactions?

A)(S)-2-Methoxypentane
B)(R)-2-Methoxypentane
C)(±)-2-Methoxypentane
D)trans-2-Butene

Question 41

Determine the product in the following reaction (ignoring possible stereoisomers).

A)I
B)II
C)III
D)IV

Question 42

What are the major products obtained upon treatment of methyl phenyl ether with excess HBr?

A)Phenol and bromomethane
B)Phenol and methanol
C)Bromobenzene and bromomethane
D)Bromobenzene and methanol

Question 43

What is the major organic product of the following reaction?

A)I
B)II
C)III
D)IV

Question 44

What is the major organic product of the following reaction?

A)I
B)II
C)III
D)IV

Question 45

What is the product of the following reaction?

A)I
B)II
C)III
D)IV

Question 46

Which of the following statements about the reaction of ethers with strong acids is true?

A)HCl, HBr, and HI can all be used.
B)The mechanism of ether cleavage is S_N1 only.
C)The mechanism of ether cleavage is S_N2 only.
D)The mechanism of ether cleavage is S_N1 and S_N2.

Question 47

What is the major alkene formed when compound A is dehydrated with POCl₃ and pyridine?

A)I
B)II
C)III
D)IV

Question 48

Determine the product in the following reaction (ignoring possible stereoisomers).

A)I
B)II
C)III
D)IV

Question 49

What is the major alkene formed when compound A is dehydrated with H₂SO₄?

A)I
B)II
C)III
D)IV